A complete mechanism for the given reaction is to be provided. Concept introduction: Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the S N 2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the − OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Question

Want to see the full answer?

Answer 1

Question

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Draw a complete, detailed mechanism for this reaction.

The reaction shown here is a halosulfonation, which is a useful variation of the sulfonation reaction. Draw the complete mechanism for this reaction.

Draw the complete, detailed mechanism for the following reaction.

Answer 2

Question

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Answer 6

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Answer 7

Chapter 10, Problem 10.47P

Interpretation Introduction

Interpretation:

A complete mechanism for the given reaction is to be provided.

Concept introduction:

Under acidic conditions, an ether is protonated converting the oxygen to a better leaving group and the adjacent carbon to an electrophile. The oxygen is bonded to a primary carbon. Therefore, its substitution will occur via the SN2 mechanism. Once the ether oxygen is protonated and converted to a better leaving group, the nucleophile ethanol will attack the adjacent carbon opening the ring. A second substitution can take place, replacing the −OH group at the other end of the opened chain by a second ethoxide to give a disubstituted product.

Answer 8

Expert Solution & Answer

Answer 9

Expert Solution & Answer

Answer 10

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 11

Ch. 10 - Prob. 10.1P Ch. 10 - Prob. 10.2P Ch. 10 - Prob. 10.3P Ch. 10 - Prob. 10.4P Ch. 10 - Prob. 10.5P Ch. 10 - Prob. 10.6P Ch. 10 - Prob. 10.7P Ch. 10 - Prob. 10.8P Ch. 10 - Prob. 10.9P Ch. 10 - Prob. 10.10P

Solution Summary: The author explains the mechanism of the cyclic ether's reaction, which involves protonation, deprotonation and a second substitution.

Concept explainers

Videos

Want to see the full answer?

Chapter 10 Solutions